Water → 1-(5-Bromo-2-fluorophenyl)propan-1-ol

HRID 1484548Notes

Reaction equation

HRID 1484548 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11]([Mg]Br)[CH3:12].O>C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:7]([OH:8])[CH2:11][CH3:12])[CH:9]=1

Participants

5

Conditions

Temperature
0 °C

Procedure

To a solution of 15 g (73.9 mmol) 5-bromo-2-fluorobenzaldehyde in diethyl ether (100 ml) at 0° C. were slowly added 27.1 ml (81.3 mmol) of ethylmagnesium bromide solution (3 M in diethyl ether). After stirring at 0° C. for 3 h, water (20 ml) was carefully added upon which a white precipitate formed. The solid was filtered off and washed with tert-butyl methyl ether. The combined filtrates were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude title compound thus obtained (16.1 g, 93% of th.) was used in the next step without further purification.

Workup

  1. customat 0° C.
  2. customformed
  3. filtrationThe solid was filtered off
  4. washwashed with tert-butyl methyl ether
  5. washThe combined filtrates were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-829751eed3804141bd8c0201d573f388
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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